CA2822016C - Synthese a basse temperature de chlorhydrate de methylphenidate - Google Patents

Synthese a basse temperature de chlorhydrate de methylphenidate Download PDF

Info

Publication number
CA2822016C
CA2822016C CA2822016A CA2822016A CA2822016C CA 2822016 C CA2822016 C CA 2822016C CA 2822016 A CA2822016 A CA 2822016A CA 2822016 A CA2822016 A CA 2822016A CA 2822016 C CA2822016 C CA 2822016C
Authority
CA
Canada
Prior art keywords
molar equivalents
reaction temperature
acid
ratio
methylphenidate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2822016A
Other languages
English (en)
Other versions
CA2822016A1 (fr
Inventor
C. Frederick M. Huntley
Knicholaus Dudley La Lumiere
Helge Alfred Reisch
Erik Wayne Kataisto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhodes Technologies Inc
Original Assignee
Rhodes Technologies Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhodes Technologies Inc filed Critical Rhodes Technologies Inc
Publication of CA2822016A1 publication Critical patent/CA2822016A1/fr
Application granted granted Critical
Publication of CA2822016C publication Critical patent/CA2822016C/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur un procédé pour la préparation de chlorhydrate de méthylphénidate. Le procédé comprend l'estérification d'acide ritalinique et de méthanol en présence d'un catalyseur acide à une basse température. Le procédé peut éventuellement comprendre l'ajout d'un orthoester.
CA2822016A 2010-12-17 2011-12-16 Synthese a basse temperature de chlorhydrate de methylphenidate Expired - Fee Related CA2822016C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201061424424P 2010-12-17 2010-12-17
US61/424,424 2010-12-17
PCT/IB2011/003140 WO2012080834A1 (fr) 2010-12-17 2011-12-16 Synthèse à basse température de chlorhydrate de méthylphénidate

Publications (2)

Publication Number Publication Date
CA2822016A1 CA2822016A1 (fr) 2012-06-21
CA2822016C true CA2822016C (fr) 2016-10-25

Family

ID=45509554

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2822016A Expired - Fee Related CA2822016C (fr) 2010-12-17 2011-12-16 Synthese a basse temperature de chlorhydrate de methylphenidate

Country Status (13)

Country Link
US (1) US9475770B2 (fr)
EP (2) EP2937336A1 (fr)
JP (1) JP5886869B2 (fr)
KR (2) KR20150029769A (fr)
CN (1) CN103298785B (fr)
AU (1) AU2011342894C1 (fr)
BR (1) BR112013015072A2 (fr)
CA (1) CA2822016C (fr)
CO (1) CO6741202A2 (fr)
ES (1) ES2542433T3 (fr)
MX (1) MX343653B (fr)
NZ (1) NZ612298A (fr)
WO (1) WO2012080834A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014024203A1 (fr) * 2012-08-07 2014-02-13 Zcl Chemicals Limited Procédé perfectionné pour la préparation de chlorhydrate de dexméthylphénidate
US9278928B2 (en) * 2012-11-29 2016-03-08 Zcl Chemicals Limited Process for the preparation of d-threo-ritalinic acid salts via novel salts of intermediate thereof
CA2928959A1 (fr) * 2013-11-08 2015-05-14 Noramco, Inc. Procede de preparation de methylphenidate et de ses sels pharmaceutiques
US20170196846A1 (en) * 2014-06-06 2017-07-13 Rhodes Pharmaceuticals, L.P. Methods for treating attention deficit hyperactivity disorder with methylphenidate
CA2936741C (fr) 2014-10-31 2018-11-06 Purdue Pharma Methodes et compositions destinees au traitement du trouble de deficit d'attention
CN104744342A (zh) * 2015-02-11 2015-07-01 河南中帅医药科技股份有限公司 盐酸右哌甲酯晶型及其制备方法
CN107325039B (zh) * 2016-04-29 2022-12-16 国药集团国瑞药业有限公司 一种盐酸右哌甲酯的制备方法
US10722473B2 (en) 2018-11-19 2020-07-28 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
CN110698341A (zh) * 2019-10-24 2020-01-17 安庆博曼生物技术有限公司 丙炔酸衍生物的环保制备方法

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2507631A (en) 1944-01-19 1950-05-16 Ciba Pharm Prod Inc Pyridine and piperidine compounds and process of making same
US2957880A (en) 1953-12-23 1960-10-25 Ciba Pharm Prod Inc Process for the conversion of stereoisomers
US2838519A (en) 1953-12-23 1958-06-10 Ciba Pharm Prod Inc Process for the conversion of stereoisomers
US4347374A (en) 1980-07-21 1982-08-31 Merck & Co., Inc. Acid addition salts of N-trityl-α-fluoromethylhistidine enantiomer derivatives
US5733756A (en) 1996-01-05 1998-03-31 Celgene Corporation Lactams and processes for stereoselective enrichment of lactams, amides, and esters
US6242464B1 (en) 1996-01-22 2001-06-05 Chiroscience Limited Single isomer methylphenidate and resolution process
GB9604943D0 (en) 1996-03-08 1996-05-08 Chiroscience Ltd Resolution
WO1998025902A1 (fr) 1996-12-13 1998-06-18 Medeva Europe Limited Preparation de threo-methylphenidate enrichi en un enantiomere
GB9700912D0 (en) * 1997-01-17 1997-03-05 Chiroscience Ltd Resolution
US5936091A (en) 1997-05-22 1999-08-10 Celgene Corporation Processes and intermediates for resolving piperidyl acetamide stereoisomers
US6548522B1 (en) 1999-10-12 2003-04-15 Hoffmann-La Roche Inc. Method for treating conditions related to the glutamate receptor using carboxylic acid amide derivatives
US7482366B2 (en) 2001-12-21 2009-01-27 X-Ceptor Therapeutics, Inc. Modulators of LXR
DE602004022633D1 (de) 2003-01-30 2009-10-01 Boehringer Ingelheim Pharma 2,4-diaminopyrimidinderivate, die sich als inhibitoren von pkc-theta eignen
CH712083B1 (de) 2003-02-05 2017-07-31 Siegfried Ag Verfahren zur Herstellung von d-threo-2-Phenyl-2-piperidin-2-yl-essigsäureestern.
US20050032873A1 (en) 2003-07-30 2005-02-10 Wyeth 3-Amino chroman and 2-amino tetralin derivatives
US7229557B2 (en) 2004-02-04 2007-06-12 Konec, Inc. Method to separate stereoisomers
BRPI0716583A2 (pt) 2006-08-24 2013-10-01 Australian Nuclear Science Tec ligandos fluorados para marcar recptores de benzodiazepina perifÉricos
US20100022446A1 (en) 2007-01-18 2010-01-28 Novo Nordisk A/S Use of Peptides in Combination with Surgical Intervention for the Treatment of Obesity
WO2010080787A1 (fr) * 2009-01-09 2010-07-15 Mallinckrodt Inc. Synthèse du méthylphénidate et des analogues de celui-ci
WO2011067783A1 (fr) * 2009-12-01 2011-06-09 Harman Finochem Limited Procédé de préparation de chlorhydrate de phénidate de méthyle

Also Published As

Publication number Publication date
US20150038720A1 (en) 2015-02-05
KR20130115322A (ko) 2013-10-21
US9475770B2 (en) 2016-10-25
BR112013015072A2 (pt) 2016-07-12
EP2651892A1 (fr) 2013-10-23
KR20150029769A (ko) 2015-03-18
WO2012080834A1 (fr) 2012-06-21
JP2014503530A (ja) 2014-02-13
CO6741202A2 (es) 2013-08-30
MX2013007020A (es) 2014-11-10
AU2011342894B2 (en) 2015-05-07
CN103298785B (zh) 2016-04-20
CN103298785A (zh) 2013-09-11
WO2012080834A8 (fr) 2012-09-13
EP2651892B1 (fr) 2015-04-22
JP5886869B2 (ja) 2016-03-16
MX343653B (es) 2016-11-07
CA2822016A1 (fr) 2012-06-21
KR101561361B1 (ko) 2015-10-16
ES2542433T3 (es) 2015-08-05
AU2011342894A1 (en) 2013-05-02
EP2937336A1 (fr) 2015-10-28
AU2011342894C1 (en) 2015-07-30
NZ612298A (en) 2014-06-27

Similar Documents

Publication Publication Date Title
CA2822016C (fr) Synthese a basse temperature de chlorhydrate de methylphenidate
US8008479B2 (en) Organic compounds
US8283472B2 (en) Synthesis of methylphenidate and analogs thereof
JP2008504302A (ja) 鏡像異性体に関して純粋なアトモキセチンとトモキセチンマンデル酸塩
JP2004520405A (ja) 非水和塩酸フェキソフェナジンの製造方法とこの方法により得ることができる新規な結晶質形態
JP2004504319A (ja) ４−フェニルピペリジン誘導体の新規製造方法
EP2486012B1 (fr) Procédé de préparation de composés de 2 (1 phényléthyl)isoindolin-1-one
EP2964210B1 (fr) Procédé pour la préparation de composés de 2-amino-1,3-propanediol et de sels de ceux-ci
EP2371817A1 (fr) Procédé pour la préparation de 1-[4-(1,1-diméthyléthyl)phényl]-4-[4-(diphénylméthoxy)-1-pipéridinyl]-1-butanone et de sels d'addition acides correspondant
US9573896B2 (en) Methods for preparing d-threo-methylphenidate using diazomethane, and compositions thereof
CZ20023694A3 (cs) Tosylátové soli 4-(p-fluorfenyl)-piperidin-3-methanolů
JP2006508110A (ja) 新規な２，３−ジヒドロ−４（１ｈ）−ピリジノン誘導体、それらの製造方法およびそれらを含む医薬組成物
US20060122227A1 (en) Process for alkylating secondary amines and the use in donepezil preparation thereof
WO2011158262A1 (fr) Forme polymorphe du chlorhydrate de fexofénadine, intermédiaires et procédé de préparation
JPH0366298B2 (fr)
KR101299720B1 (ko) 3-아미노-5-플루오로-4-디알콕시펜탄산 에스테르의 새로운제조방법
EP2765131B1 (fr) Procédé de production de monoxidine
JP2011526257A (ja) Ｎ−フェニル−ｎ−（４−ピペリジニル）アミド塩の製造方法
NL1037485A (nl) Levocetirizine by menthyl intermediate.
JP4441260B2 (ja) ４−アミノ−４−フェニルピペリジン類の製造方法
EP2177221A1 (fr) Procedure de préparation de répaglinide essentielment optiquement pur et ses précurseurs
WO2001004113A2 (fr) Nouveau processus
JP2007197397A (ja) 多置換エチレンジアミン誘導体の製造方法
FR2983197A1 (fr) Utilisation de phacetoperane pour traiter un trouble deficit de l'attention hyperactivite

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20130617

MKLA Lapsed

Effective date: 20211216